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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 279018Generated: October 30, 2026

2-Benzyloxy-5-cyano-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione → 5-Cyano-2-hydroxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione

https://huagongshe.com/reaction/279018

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-Benzyloxy-5-cyano-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dioneHCID 22623971—
ReactantHCID 178418361HCID 178418361—
CatalystPd barium sulfateHCID 16218511—
SolventTetrahydrofuranHCID 8028—
Product5-Cyano-2-hydroxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dioneHCID 2262397845.9%

Reaction Steps

A mixture of 2-benzyloxy-5-cyano-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.16 g, 0.40 mmol, from Example D2) and 5% Pd/BaSO4 (0.05 g) in THF (75 mL) was shaken in an atmosphere of hydrogen at 50 psi at ambient temperature for 86 hours with an additional 0.05 g of 5% Pd/BaSO4 being added after 70 hours. The catalyst was removed by filtration and the filtrate evaporated under reduced pressure. The residue was chromatographed on silica using chloroform/methanol (10:1) to give 0.059 g of the title compound, mp >250° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06362181B1
Source datasetuspto-grants-2002_03
ORD IDord-04d0c76f074749d4a8b44bf59eb3c932
Source noteuspto-grants-2002_03